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The reaction of 3-chlorocarbonyl derivatives of bile acid esters with O,O-, N,N-, and S,S-dinucleophiles provides a general and efficient entry into steroid dimers with bis-carbamate, bis-carbonate, and bis-monothiocarbonate moieties in the linker fragment. The macrocyclization of the bis-carbamate 10 afforded the dimeric and tetrameric cholaphanes, 15 and 16, respectively.
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